Hydrochloric Acid → (1H-benzoimidazol-2-yl)-{3-[3-(1,2,3,6-tetrahydro-pyridin-4-yl)-pyrazin-2-yl]-azetidin-1-yl}-methanone hydrochloride

HRID 1850331Notes

Reaction equation

HRID 1850331 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:19]([CH:20]3[CH2:23][N:22]([C:24]([C:26]4[NH:30][C:29]5[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=5[N:27]=4)=[O:25])[CH2:21]3)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:35]>CO>[ClH:35].[NH:27]1[C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=[C:26]1[C:24]([N:22]1[CH2:21][CH:20]([C:19]2[C:14]([C:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=3)=[N:15][CH:16]=[CH:17][N:18]=2)[CH2:23]1)=[O:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 585468644-{3-[1-(1H-benzoimidazole-2-carbonyl)-azetidin-3-yl]-pyrazin-2-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67469099(1H-benzoimidazol-2-yl)-{3-[3-(1,2,3,6-tetrahydro-pyridin-4-yl)-pyrazin-2-yl]-azetidin-1-yl}-methanone hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 4-{3-[1-(1H-Benzoimidazole-2-carbonyl)-azetidin-3-yl]-pyrazin-2-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (217 mg, 0.47 mmol) was added 4 M HCl in MeOH (100 mL). The solution was stirred at RT for 2 h. The solvent was removed under reduced pressure to give (1H-benzoimidazol-2-yl)-{3-[3-(1,2,3,6-tetrahydro-pyridin-4-yl)-pyrazin-2-yl]-azetidin-1-yl}-methanone hydrochloride (187 mg, 0.47 mmol, yield 100%). ESI-MS (M+1): 361 calc. for C20H20N6O 360.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4075efc4ad8e4301a45dcc1f190de056
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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